Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C-3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core

Mughal E, Neumann B, Stammler H-G, Zhi WL, Wei J, Kuck D, Cao X (2015)
European Journal of Organic Chemistry (13): 2835-2847.

Journal Article | Published | English

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Abstract
The syntheses and structural properties of novel triscyclophanes that bear the rigid, bowl-shaped tribenzotriquinacene (TBTQ) core are reported. Condensation of the 2,3,6,7,10,11-hexakis(chloromethyl) derivative with catechols and 1,2-benzenedithiol gives rise to elongation of the three indane wings (intra-wing extension), whereas incorporation of resorcinol, hydroquinone, and 1,3- and 1,4-benzenedithiol units occurs by bridging the 3D bays of the TBTQ framework (inter-wing extension), yielding TBTQ-based cavitands. Constitutional and conformational details were studied by X-ray diffraction, VT-NMR spectroscopy, and molecular modeling. The bay-bridged TBTQ-based triscyclophanes bearing 1,3-dioxy-and 1,3-dithiophenylene units adopt globular and cone-like C-3-symmetrical shapes, respectively, with limited conformational flexibility. Baybridging by 1,4-dioxy- and 1,4-dithiophenylene units generates a more complanate coverage of the bowl face with even less conformational flexibility.
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Mughal E, Neumann B, Stammler H-G, et al. Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C-3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core. European Journal of Organic Chemistry. 2015;(13):2835-2847.
Mughal, E., Neumann, B., Stammler, H. - G., Zhi, W. L., Wei, J., Kuck, D., & Cao, X. (2015). Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C-3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core. European Journal of Organic Chemistry(13), 2835-2847.
Mughal, E., Neumann, B., Stammler, H. - G., Zhi, W. L., Wei, J., Kuck, D., and Cao, X. (2015). Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C-3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core. European Journal of Organic Chemistry, 2835-2847.
Mughal, E., et al., 2015. Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C-3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core. European Journal of Organic Chemistry, (13), p 2835-2847.
E. Mughal, et al., “Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C-3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core”, European Journal of Organic Chemistry, 2015, pp. 2835-2847.
Mughal, E., Neumann, B., Stammler, H.-G., Zhi, W.L., Wei, J., Kuck, D., Cao, X.: Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C-3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core. European Journal of Organic Chemistry. 2835-2847 (2015).
Mughal, Ehsan, Neumann, Beate, Stammler, Hans-Georg, Zhi, Wei Li, Wei, Jun, Kuck, Dietmar, and Cao, Xiaoping. “Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C-3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core”. European Journal of Organic Chemistry 13 (2015): 2835-2847.
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